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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 13-14
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Original Articles

Chiral Organosiucon Compounds. Part 1. Synthesis of Chiral Silyl Enol Ethers

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Pages 2337-2343 | Received 08 Mar 1989, Published online: 24 Oct 2006

References

  • Walkup , R. D. 1987 . Tetrahedron Lett. , 28 ( 5 ) : 511
  • Walkup , R. D. and Obeyesekere , N. H. 1988 . J. Org. Chem. , 53 ( 4 ) : 920
  • Fractional distillation of the crude product obtained following the reported method (Reference 1) afforded, as the major components, the bis-substituted silanes (2) [b. p. 130–134°/0.4 mmHg, σ H(500 MHz; CDCl3) 0.10(6H,S), 0.72 (6H,d), 0.82(2H, m), 0.88(12H, hd), 0.93(2H,m), 1.02(2H,q), 1.14(2H, m), 1.35 (2H, m), 1.54–1.67 (4H, m), 1.94 (2H, m). 2.17 (2H, m), and 3.5(2H,dt); °C(125 MHz : CDCl3)-1.3 (q), 15.9 (q). 21.2 (q), 22.2 (q). 22.9 (t) 25.3 (d). 31.7 (d), 34.6 (t) 45.5 (t). 50.0 (d), and 72.4 (d); v max (liquid film) 1250 and 1065 cm−1; m/z 368(M +, 60%) and 75 (100%) (Found: M +, 358.3111.C22H44O2Si requires M +, 368.3114) J and (3) [b. p. 94–96°/0.4mmHg; δH(500 MHz; CDCl3) 0.20 (6H,s). 1.49 (4H,m), 1.64 (4H,m), 2.00 (8H,m) and 4.97 (2H,m); δC(125 MHz;CDCl3)-2.1 (q), 22.3 (t), 23.1 (t), 23.8 (t), 29.5 (t), 105.5 (d), 149.5 (s); v max (liquid film) 1650, 1250, and 1170 cm−1; m/z 252 (M +, 30%) and 75 (100%) (Found: M +, 252.1550.C14H24O2Si requires M +, 252.1546)].
  • Concentrations of the bis(alkoxy)silane (2) were typically estimated by g. l. c. to be less than 10%.
  • Gillard , J. W. , Fortin , R. , Morton , H. E. , Yoakim , C. , Quesnelle , C. , Daignault , S. and Guindon , Y. 1988 . J. Org. Chem. , 11 : 53 2602 In some cases, however, samples dispatched for high field NMR analysis gave indications of decomposition. The relative stability of alkoxy- and chlorosilanes has also been reported by
  • This reactive intermediate gave satisfactory IR, MS, and 1H NMR spectra, as did the analogous (bornyloxy)chlorodimethylsilane, which was used to prepare compounds 1(f, g).

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